Superbosses and Self-Assessment

Every industry has its leading lights, its superstars, its innovators. For ours, names like Bjarne Stroustrup, James Gosling, and Guido van Rossum come to mind. But while each of these is impressive in terms of what they have done themselves, other names from other industries highlight what we currently lack: the concept of the superboss, the manager who knows how to help talented people accomplish more than they ever dreamed was possible, and in the process develops a talent machine that makes almost everyone who enters the superboss’ orbit a star. Journalism had Gene Roberts. American football had Bill Walsh. Hollywood had Roger Corman. Real estate had Bill Sanders. Wine had Robert Mondavi. And comedy television? Jon Stewart. Each of these people became a “spawning point” for the great talent of their industry, by taking people under their wing, teaching and coaching them, and turning them back out into their industry to shine in their own right.

As a goal for us as engineering managers, it’s not a bad one to have.

While the subject of the superboss is far greater than what we can cover in a single section of a single chapter, it’s fortunate that there’s a book—Superbosses, by Sydney Finkelstein—that covers it in greater detail for those who are interested. As a quick intro, a superboss exhibits several interesting character traits:

• Extreme confidence. “There are no problems, only solutions.” The superboss has a deep, almost extreme level of confidence in their abilities, which sometimes bleeds over into areas in which they aren’t known for their expertise. (Intel cofounder Robert Noyce was a pilot, an active heli-skier, and a motorcycle enthusiast known to race through Bali streets in a monsoon.)
• Competitiveness. Superbosses thrive on it, they seek it out, and they create it. It doesn’t have to be competitiveness against others—sometimes it’s against themselves, always looking to find better ways to do whatever task is at hand, even if it’s just doing the dishes.
• Imagination. Superbosses have a strong imagination, and often use that to help drive their visions of what they want to accomplish. They live the idea that “If you can dream it, you can build it.”
• Integrity. Superbosses have a strict adherence to a core vision or sense of self, and aren’t distracted by the need to satisfy large egos. They want to see the vision through, not see themselves on a pedastal.
• Authenticity. The superboss doesn’t pretend to be any different for their reports than they are away from the office. In their daily interactions with others, they let their personalities show.

If you’re around people like this, much less having one for your boss, you really can’t help but be energized.

If you want to work to be one of these, start with this 10-point questionnaire, and after answering the questions as honestly as you can, reflect on how you can be better about some of the subjects raised here. (And pick up the book, it’s a great read.)

1. Do you have a specific vision for your work that energizes you, and that you can use to energize and inspire your team?
2. How often do people leave your team to accept a bigger offer elsewhere? What’s that like when it happens?
3. Do you push your reports to meet only the formal goals set for the team, or are there other goals that employees sometimes also strive to achieve?
4. How do you go about questioning your own assumptions about the business? How do you get your team to do the same about their own assumptions?
5. How do you balance the need to delegate responsibilities to team members with the need to provide hands-on coaching to them? How much time do you usually spend coaching employees?
6. When promoting employees, do you ever put them into challenging jobs where they potentially might fail? If so, how do you manage the potential risk? And what happens if they do fail? (This will usually only apply to second-level and above managers, though you can approximate some of this as a first-level manager with some of the tactics we discuss later in this chapter.)
7. How much affection or connection do members of your team feel with one another? Do people tend to spend time out of the office socializing? What is the balance of competition and collaboration on the team?
8. Do you continue to stay in touch with employees who have left to work elsewhere?
9. Have any former employees of yours gone on to have particularly noteworthy careers, either here or elsewhere? If so, how many? Any examples?
10. What is the culture like on your team with respect to how much energy you devote to nurturing or developing individuals versus getting the job done?

Some of these will be questions to mull over and have in the back of your mind as you develop your career as an engineering manager (and whatever follows), but there are some things you can start doing right now to start building that culture of superboss-ness that sets the foundation for future excellence.